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Choosing the wrong wedding venue in Tuscany: A real story with a happy ending

May 27, 2026

Choosing the wrong wedding venue in Tuscany: A real story with a happy ending

Helen&Matt’s Wedding in Villa Mocale
A real case study on why starting from the venue is one of the most common and expensive mistakes couples make

There’s a moment I’ve seen more than once in my work as a wedding planner, way too many times

A couple walks in in my Magnolia world: excited, organized, clearly not the type to leave things to chance
They’ve done their researches
They’ve visited venues
They’ve narrowed down the list
They have a favorite, the one their lil hearts fall in love with
Helen & Matt were one of these couples:  they arrived with a venue contract already on the table just ready to be signed (and deposit to be paid)

They weren’t asking me to help them choose. They were asking me to help them execute.

Which has ever been fine to me
Except I knew that venue really well and it wasn’t at all their best match

And that’s where things got complicated
REALLY COMPLIMENTED MEHH

Bride and groom walking together in the Tuscan countryside surrounded by cypresses during their destination wedding in Tuscany

What a website (and not even a visit) cannot tell you

Here’s the thing about the first initial venue: it wasn’t a bad place at all !  It was actually a beautiful property.
They had visited, walked the grounds, seen the spaces, talked with the manager, tasted the food and genuinely loved it, immensely

The problem was something that hadn’t been considered by anyone involved, including the villa’s own team, cause they cannot know all your vision my loves, it’s part of an upper layer of work they are not involved in

The property is a Villa yes, but an hotel Villa in Florence
Being not only a wedding venue, if it’s not booked in exclusive use, which was something Helen&Matt were not interested into, andhaving guests in rooms that have nothing to do with their wedding.. things were not fully smooth
Logically this meant the curfew wasn’t arbitrary or negotiable, guests of the hotel had the right to sleep with no hard party going on, of course

Was this clear to Helen & Matt? No

No one had flagged this. Not the couple, because they didn’t know what questions to ask. Not the villa’s manager either, because, and this is something couples need to be aware of,  venue managers are not wedding planners.
They know their property, but they don’t know you, your vision, your project and your possible next steps

The curfew would have cut the evening at exactly the wrong moment.

But there was more

When talking with Helen&Matt about the Villa contingency plan for bad weather (which is a non-negotiable topic as yes my loves it can rain even in summer in Tuscany) there was an indoor plan and it wasn’t vague, it was (it is) a beautiful one, but not big enough for the number of guests they were inviting
And as the venue was not supposed to be booked from the couple in exclusive use, the main lawn could not hosted a big tent

No way to create what they needed if the sky didn’t cooperate
Again: not the villa’s fault

Simply the vision and needs weren’t matching with what the venue would have included in the contract for them

As I was going through these details with the couple, a thought kept surfacing: how had all of this gone unnoticed?
How had they gotten to the contract stage without any of this surfacing?

The answer is the one I keep coming back to in this work. They trusted the process, the way most couples do.
They visited, they asked questions, they got answers.
Period.

But the questions a couple knows to ask are limited by what a couple already know, which is counterintuitive, but so true.

And a venue manager, however professional and well-intentioned, cannot fill that gap.

That’s not their job. It’s mine.

Wedding ceremony in Villa Florence Tuscany white and light blue botanical style

The Conversation I Had to Have

Telling a couple that the venue they’ve fallen in love with isn’t going to work is not a comfortable conversation. AT ALL
There’s no good way to soften it completely.

I was honest, there is no other way around this
I walked them through everything not matching their needs (and wishes)  explained why each point mattered and what it would concretely mean for their wedding day. The curfew alone would have cut the evening short at a crucial moment. The weather risk, without a proper backup, was something I wasn’t willing to leave to chance.

Their reaction?
AH

Exactly what you’d expect -_-

After a few weeks, we realized that things weren’t going to work out at our first venue and we started to enter panic mode

Their words, not mine and they said it themselves in the review they left me afterward. (you can see it here in full )

And that’s okay. Yes really ok
Panic is a reasonable response when something you thought was settled, suddenly isn’t

My job in that moment wasn’t to tell them not to worry
It was to give them something concrete to hold onto instead

Cocktail Aperitivo Wedding in Villa in Chianti Tuscany , Wedding Planner Tuscany

The Turn

Before the “panic” call was over, I had already pulled out 1 venue that I knew would have been perfect for them: not just aesthetically, but operationally and stylistically and visually and emotionally and… ok perfect
And it was a REAL love : Villa Mocale.

It wasn’t a backup at all

The space worked for their guest count and flow. The curfew wasn’t an issue. There was a real contingency plan for weather.
The team there was experienced and collaborative and the date was available.

I came to them not just with a problem, but with a solution that was already mapped out
Availability confirmed. Preliminary quote ready. A clear path forward

They made the decision to let go of the first venue. It wasn’t easy, they’d been emotionally attached to it, but they trusted the process, and they moved forward.

Wedding dinner al fresco in Medicean Villa Florence, Chianti Tuscany

What Happened Next

From that point on, everything shifted.
The weight of uncertainty lifted and they could finally start enjoying what wedding planning is actually supposed to feel like: creative, exciting, joyful

We spent the following months building theri wonderful Wedding in Tuscany together. Vendors chosen with intention. Every detail considered. Every doubt addressed before it had a chance to become a problem.

On May 3rd, they got married and it was a dream!

It was one of the deepest weddings I’ve been part of. Not because everything was perfect in some abstract sense, but because every decision had been made with clarity and awareness: THEY WERE AWARE
There were no last-minute surprises.
No compromises they hadn’t agreed to.
Just a day that felt entirely like them

oh oh don’t go… it’s not all :)

THE LESSON TO LEARN

The lesson behind this story,  why starting from the venue is one of the most common mistakes couples make and what to do instead  is something I want to explore properly.
I’m recording a video about it,and it’s coming soon.

IN THE MEANTIME

If you’re in the early stages of planning your wedding and you already have a venue in mind  or a contract on the table  I’d love to talk before you sign anything

Get in touch →

MY WONDERFUL TEAM

Villa in Tuscany Villa Mocale.
Caterer in Tuscany Ciabatti Ricevimenti
Bar Pour Events
Photographer Antonella Cati PH
MUAH Valentina Corrias
Flowers Silvia Mattera Alchemy Bloom
Strings musicians PBWeddings
DJ Betto DJ

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